Citation: Lian ZENG, Yu-He JIANG, Jin-Ting WU, Hong-Bo LI, Jian-Guo ZHANG. Molecular Design and Performance Studies of 4-(1, 2, 4-Triazole-5-yl) Furazan Derivatives as Promising Energetic Materials[J]. Chinese Journal of Structural Chemistry, ;2021, 40(7): 942-948. doi: 10.14102/j.cnki.0254–5861.2011–3061 shu

Molecular Design and Performance Studies of 4-(1, 2, 4-Triazole-5-yl) Furazan Derivatives as Promising Energetic Materials

Lian ZENG ^a ,
Yu-He JIANG ^a ,
Jin-Ting WU ^{a, b,,} ,
Hong-Bo LI ^a,, ,
Jian-Guo ZHANG ^b

a.
School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China
b.
State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, China

Corresponding author: Jin-Ting WU, wjt1234@163.com Hong-Bo LI, li-honggg@163.com
Received Date: 10 December 2020
Accepted Date: 25 January 2021

Fund Project: the Opening Project of State Key Laboratory of Explosion Science and Technology (Beijing Institute of Technology) KFJJ20-03MDoctoral Foundation of SWUST 17zx7128Major Special Projects of the Equipment Development Department of the Central Military Commission of China 14021001040305-5

Figures(5)

In this paper, eight 4-(1, 2, 4-triazole-5-yl) furazan (TZFZ) derivatives were designed, and the molecular configurations of TZFZ compounds were optimized by using the B3LYP/6-311+G* level. Meanwhile, the detonation performance, density, impact sensitivity, heat of formation and oxygen balance have been investigated. The results clearly and intuitively illustrate that the introduction of -NO₂ and coordination oxygen plays a pivotal role in increasing the density and heat of formation. In summary, the properties of these compounds are better than the traditional explosives RDX and TNT, especially the density and detonation pressure. Energetic evaluations showed that compounds B1 (P = 36.73 GPa; D = 8.98 km·s^-1, ρ = 1.88 g·cm^-3) and B7 (P = 38.51 GPa; D = 9.17 km·s^-1, ρ = 1.90 g·cm^-3) could be seen as promising candidates of energetic insensitive compounds with remarkable performance.
- density functional theory,
- 4-(1, 2, 4-triazole-5-yl)furazan derivatives,
- performance prediction,
- molecular design
1. [1]
  Yu, Q.; Yang, H. W.; Imler, G. H.; Parrish, D. A.; Cheng, G. B.; Shreeve, J. M. Derivatives of 3, 6-bis(3-aminofurazan-4-ylamino)-1, 2, 4, 5-tetrazine: excellent energetic properties with lower sensitivities. Acs. Appl. Mater. Inter. 2020, 12, 31522−31531. doi: 10.1021/acsami.0c08526
2. [2]
  Malow, M.; Wehrstedt, K. D.; Neuenfeld, S. On the explosive properties of 1H-benzotriazole and 1H-1, 2, 3-triazole. Tetrahedron Lett. 2007, 48, 1233−1235. doi: 10.1016/j.tetlet.2006.12.046
3. [3]
  Li, X. H.; Zhang, R. Z.; Zhang, X. Z. Theoretical studies on a series of 1, 2, 3-triazoles derivatives as potential high energy density compounds. Struct. Chem. 2011, 22, 577−587. doi: 10.1007/s11224-011-9734-y
4. [4]
  Jin, R. Y.; Zeng, C. Y.; Liang, X. H.; Sun, X. H.; Liu, Y. F.; Wang, Y. Y.; Zhou, S. Design, synthesis, biological activities and DFT calculation of novel 1, 2, 4-triazole Schiff base derivatives. Bioorg. Chem. 2018, 80, 253−260. doi: 10.1016/j.bioorg.2018.06.030
5. [5]
  Du, L. X. S.; Liu, Y. C.; Cheng, G. M.; Luo, J. Molecular design and property study of xifurza type fused cast explosive. Acta Armamentarii 2018, 39, 46−56. doi: 10.3969/j.issn.1000-1093.2018.01.005
6. [6]
  Jin, X. H.; Zhou, J. H.; Hu, B. C. Exploration of high-energy-density materials: computational insight into energetic derivatives based on 1, 2, 4, 5-tetrahydro-1, 2, 4, 5-tetrazine. Chemistryopen 2018, 7, 780−788. doi: 10.1002/open.201800161
7. [7]
  Sun, S. Y.; Lu, M. Conjugation in multi-tetrazole derivatives: a new design direction for energetic materials. J. Mol. Model. 2018, 24, 173−182. doi: 10.1007/s00894-018-3710-z
8. [8]
  Dalinger, I. L.; Kormanov, A. V.; Suponitsky, K. Y.; Muravyev, N. V.; Sheremetev, A. B. Pyrazole-tetrazole hybrid with trinitromethyl, fluorodinitromethyl, or (difluoroamino) dinitromethyl groups: high-performance energetic materials. Chem. Asian J. 2018, 13, 1165−1172. doi: 10.1002/asia.201800214
9. [9]
  Xu, Z.; Cheng, G.; Yang, H.; Zhang, J.; Shreeve, J. N. M. Synthesis and characterization of 4-(1, 2, 4-triazole-5-yl)furazan derivatives as high-performance insensitive energetic materials. Chem. Eur. J. 2018, 24, 10488−10497. doi: 10.1002/chem.201801597
10. [10]
  Zhai, L. J.; Wang, B. Z.; Fan, X. Z. Synthesis and property estimation of 3, 3΄-bis (tetrazole-5-yl)-4, 4΄-azotaxime. Chin. J. Explos. Propellants 2016, 41, 21−25.
11. [11]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B. 01, Gaussian, Inc., Pittsburgh PA 2003.
12. [12]
  Politzer, P.; Martinez, J.; Murray, J. S.; Concha, M. C.; Toro-Labbe, A. An electrostatic interaction correction for improved crystal density prediction. Mol. Phys. 2009, 107, 2095−2101. doi: 10.1080/00268970903156306
13. [13]
  Politzer, P.; Murray, J. S. Some perspectives on estimating detonation properties of C, H, N, O compounds. Cent. Eur. J. Energ. Mater. 2011, 8, 209−220.
14. [14]
  Kamlet, M. J.; Ablard, J. E. Chemistry of detonations. II. Buffered equilibria. J. Chem. Phys. 1968, 48, 36−42. doi: 10.1063/1.1667930
15. [15]
  Kamlet, M. J.; Dickinson, C. Chemistry of detonations. III. Evaluation of the simplified calculational method for Chapman-Jouguet detonation pressures on the basis of available experimental information. J. Chem. Phys. 1968, 48, 43−50. doi: 10.1063/1.1667939
16. [16]
  Kamlet, M. J.; Jacobs, S. J. Chemistry of detonations. I. A simple method for calculating detonation properties of C–H–N–O explosives. J. Chem. Phys. 1968, 48, 23−35. doi: 10.1063/1.1667908
17. [17]
  He, P.; Zhang, J. G.; Wu, L.; Wu, J. T.; Zhang, T. L. Computational design and screening of promising energetic materials: novel azobis(tetrazoles) with ten catenated nitrogen atoms chain. J. Phys. Org. Chem. 2016, 30, 36−74.
18. [18]
  Rice, B. M.; Hare, J. J. A quantum mechanical investigation of the relation between impact sensitivity and the charge distribution in energetic molecules. J. Phys. Chem. 2002, 106, 1770−1783. doi: 10.1021/jp012602q
19. [19]
  Lu, T.; Chen, F. Multiwfn: a multifunctional wavefunction analyzer. J. Comput. Chem. 2012, 33, 580−592. doi: 10.1002/jcc.22885
20. [20]
  Byrd, E. F. C.; Rice, B. M. Improved prediction of heats of formation of energetic materials using quantum mechanical calculations. J. Phys. Chem. 2006, 110, 1005−1013. doi: 10.1021/jp0536192
21. [21]
  Joo, Y. H.; Shreeve, J. M. High-density energetic mono-or bis(oxy)-5-nitroiminotetrazoles. Angew. Chem. Int. Ed. 2010, 49, 7320−7323. doi: 10.1002/anie.201003866
22. [22]
  Lewczuk, R.; Ksiazek, M.; Katarzyna, G. S.; Katarzyna, C. Azo-linked high-nitrogen energetic materials. J. Mater. Chem. A 2018, 6, 1915−1940. doi: 10.1039/C7TA09593G
23. [23]
  Wu, Q.; Zhu, W.; Xiao, H. Molecular design of trinitromethyl-substituted nitrogen-rich heterocycle derivatives with good oxygen balance as high-energy density compounds. Struct. Chem. 2013, 24, 1725−1736. doi: 10.1007/s11224-013-0217-1
24. [24]
  Wei, T.; Wu, J.; Zhu, W.; Zhang, C.; Xiao, H. Characterization of nitrogen-bridged 1, 2, 4, 5-tetrazine-furazan-and 1H-tetrazole-based polyheterocyclic compounds: heats of formation, thermal stability, and detonation properties. J. Mol. Model. 2012, 18, 3467−3479. doi: 10.1007/s00894-012-1357-8
25. [25]
  Lian, P.; Lai, W. P.; Lu, J.; Liu, Y. Z.; Wei, T.; Wang, B. Z. Study on density functional theory of trifurozan oxyheterocyclic hepttriene. Comput. Appl. Chem. 2016, 33, 910−914.
26. [26]
  Ghule, V. D. Computational studies on the triazole-based high energy materials. Comput. Theor. Chem. 2012, 992, 92−96. doi: 10.1016/j.comptc.2012.05.007
27. [27]
  Li, J. A multivariate relationship for the impact sensitivities of energetic N-nitrocompounds based on bond dissociation energy. J. Hazard. Mater. 2010, 174, 728−733. doi: 10.1016/j.jhazmat.2009.09.111
28. [28]
  Zhang, C. Y. Review of the establishment of nitro group charge method and its applications. J. Hazard. Mater. 2009, 161, 21−28. doi: 10.1016/j.jhazmat.2008.04.001
1. [1]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
2. [2]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
3. [3]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
4. [4]
  Xu Huang , Kai-Yin Wu , Chao Su , Lei Yang , Bei-Bei Xiao . Metal-organic framework Cu-BTC for overall water splitting: A density functional theory study. Chinese Chemical Letters, 2025, 36(4): 109720-. doi: 10.1016/j.cclet.2024.109720
5. [5]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
6. [6]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
7. [7]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
8. [8]
  Qingyun Hu , Wei Wang , Junyuan Lu , He Zhu , Qi Liu , Yang Ren , Hong Wang , Jian Hui . High-throughput screening of high energy density LiMn_1-xFe_xPO₄ via active learning. Chinese Chemical Letters, 2025, 36(2): 110344-. doi: 10.1016/j.cclet.2024.110344
9. [9]
  Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO₄⁻, ReO₄⁻). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
10. [10]
  Xixian Sun , Shengke Li , Ruibing Wang , Leyong Wang . Functional macrocyclic arenes with active binding sites inside cavity for biomimetic molecular recognition. Chinese Chemical Letters, 2025, 36(4): 110806-. doi: 10.1016/j.cclet.2024.110806
11. [11]
  Longsheng Zhan , Yuchao Wang , Mengjie Liu , Xin Zhao , Danni Deng , Xinran Zheng , Jiabi Jiang , Xiang Xiong , Yongpeng Lei . BiVO₄ as a precatalyst for CO₂ electroreduction to formate at large current density. Chinese Chemical Letters, 2025, 36(3): 109695-. doi: 10.1016/j.cclet.2024.109695
12. [12]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
13. [13]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
14. [14]
  Zhe Wang , Li-Peng Hou , Qian-Kui Zhang , Nan Yao , Aibing Chen , Jia-Qi Huang , Xue-Qiang Zhang . High-performance localized high-concentration electrolytes by diluent design for long-cycling lithium metal batteries. Chinese Chemical Letters, 2024, 35(4): 108570-. doi: 10.1016/j.cclet.2023.108570
15. [15]
  Rui Wang , Yuan Tian , Xuefeng Gao , Lei Jiang . Design and fabrication of triangle-pattern superwettability hybrid surface with high-efficiency condensation heat transfer performance. Chinese Chemical Letters, 2025, 36(3): 110395-. doi: 10.1016/j.cclet.2024.110395
16. [16]
  Jiajun Wang , Guolin Yi , Shengling Guo , Jianing Wang , Shujuan Li , Ke Xu , Weiyi Wang , Shulai Lei . Computational design of bimetallic TM₂@g-C₉N₄ electrocatalysts for enhanced CO reduction toward C₂ products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050
17. [17]
  Yan Cheng , Hua-Peng Ruan , Yan Peng , Longhe Li , Zhenqiang Xie , Lang Liu , Shiyong Zhang , Hengyun Ye , Zhao-Bo Hu . Magnetic, dielectric and luminescence synergetic switchable effects in molecular material [Et₃NCH₂Cl]₂[MnBr₄]. Chinese Chemical Letters, 2024, 35(4): 108554-. doi: 10.1016/j.cclet.2023.108554
18. [18]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
19. [19]
  Guiyang Zheng , Xuelian Kang , Haoran Ye , Wei Fan , Christian Sonne , Su Shiung Lam , Rock Keey Liew , Changlei Xia , Yang Shi , Shengbo Ge . Recent advances in functional utilisation of environmentally friendly and recyclable high-performance green biocomposites: A review. Chinese Chemical Letters, 2024, 35(4): 108817-. doi: 10.1016/j.cclet.2023.108817
20. [20]
  Huanyan Liu , Jiajun Long , Hua Yu , Shichao Zhang , Wenbo Liu . Rational design of highly conductive and stable 3D flexible composite current collector for high performance lithium-ion battery electrodes. Chinese Chemical Letters, 2025, 36(3): 109712-. doi: 10.1016/j.cclet.2024.109712

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(358)
HTML views(9)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142